Dead Cap Table - 4/9

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• April 16 – Virtual – Bolt.new x Hustle Fund Webinar: Elizabeth Yin sits down with Eric Simons, co-founder and CEO of Bolt.new, to talk about what it's like to stare down a shutdown and come out the other side. Real talk, live Q&A, no fluff.

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How a 3× Founder (Acquired by Amplitude) Decides His First 10 Hires

Are you hiring because you need someone — or because things are starting to break?

Rippling turned one of their most-requested sessions with Patrick Thompson (3× founder, CEO of Clarify) into a practical guide you can use this week.

⬇ Download the Founder Guide: Your First 10 Hires

Patrick has used these exact frameworks across multiple startups (including one acquired by Amplitude) to build high-performing teams without bloating headcount. Inside:

• The 3-stage hiring sequence for employees #1–10

• The Barrels vs. Ammo framework to spot force-multipliers vs. executors

• How to know when NOT to hire

• Interview questions that surface real ownership

P.S. Rippling is hosting a small NYC Founders Breakfast at Hudson Yards on 4/16

*this is sponsored.

📰 Today's Edition:

Picture this nightmare scenario:

You started your company with a handshake and big dreams. 50/50 co-founders, ready to change the world.

Two years later, your co-founder drops a bomb: "I'm taking a job at Google. I don't believe in this company anymore.

Here's the kicker: He/she is fully vested on half their stock. That's 25% of your cap table walking out the door.

And you want that equity back.

Why Dead Equity Kills Startups

Dead cap table space isn't just awkward.

It's a structural problem that can literally kill your company.

The dilution math becomes brutal. When 25% of your cap table is held by someone who left two years in, every subsequent fundraise punishes the people actually building the company.

Recruiting becomes impossible. Try explaining to a world-class VP of Engineering why they're getting 0.5% when someone who left years ago sits on 25%.

Top talent can do that math. And it doesn't look fair.

Investors get nervous. VCs hate messy cap tables. They'll ask: "Why does this absent person own 20%? Can they block future rounds?"

Prevention Is Everything

The best time to solve this problem was at founding.

The second best time is now.

Four-year vesting with a one-year cliff should be standard for ALL founders. Yes, this feels weird when it's just you and your co-founder in a garage. But the cliff ensures someone who leaves in month six doesn't walk away with meaningful equity.

Include repurchase rights. Your founders' agreements should include the company's right to buy back unvested shares at cost if someone leaves.

Double-trigger acceleration is your friend. Don't let departed founders get windfall acceleration just because your company gets acquired.

Your Options When It's Too Late

So you didn't have proper vesting or people have vested across 4 years and now you’re just figuring out something that works. What now?

Option 1: Negotiate a voluntary buyback. Your departing co-founder may sell shares back at fair market value, a discount, or even their original investment.

Option 2: Invoke repurchase rights if you have them. Check your agreements carefully.

Option 3: Accept it and manage around it. Be transparent with future hires. Focus on building value so aggressively that everyone still wins despite the dead weight.

Option 4: Restructure at your next fundraise. Some investors will help clean up cap tables as part of a new round.

The Technical Details That Matter

If you're structuring a buyback, watch out for QSBS treatment.

Qualified Small Business Stock under Section 1202 allows up to 100% exclusion of capital gains – but if the company redeems shares directly, it can disqualify this benefit for everyone.

The safer move? Arrange a secondary sale to existing investors rather than a company buyback.

TL;DR

For those who stay: Be fair, but protect the company and the team still building.

For those who leave: Recognize that equity rewards future value creation, not just past effort.

For everyone: Get proper legal counsel, implement vesting from day one, and have hard conversations early before they become crises.

Your cap table isn't just paperwork – it's the foundation of alignment that can propel your company forward or drag it down.

Dunky, the flying hippocorn

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